US3410821A - Mass-coloration for polyester resins - Google Patents

Mass-coloration for polyester resins Download PDF

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Publication number
US3410821A
US3410821A US535662A US53566266A US3410821A US 3410821 A US3410821 A US 3410821A US 535662 A US535662 A US 535662A US 53566266 A US53566266 A US 53566266A US 3410821 A US3410821 A US 3410821A
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anhydride
parts
radicals
coloration
mass
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US535662A
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Cooper Albert Charles
White David Frederick
Wilkinson Donold Graham
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles

Definitions

  • This invention relates to a coloration process and more particularly to a process for the mass coloration of synthetic linear polyesters, particularly polyethylene terephthalate.
  • a and B represents a 1:2-phenylene radical and the other of A and B represents a 1:2-phenylene, 1:2- naphthylene, 2:3-naphthylene, 1:8-naphthylene or a 1:8- acenapthylene radical, and the said radicals together contain at least one group of the formula:
  • R represents a hydrogen atom or an alkyl, hydroxyalkyl or alkoxyalkyl radical
  • X represents an alkylene or phenylene radical
  • n represents 1 or 2
  • a and B optionally contain further substituents other than sulphonic acid groups.
  • alkylene radicals represented by X are preferably lower alkylene radicals containing from 1 to 6 carbon atoms, and as examples of such radical-s there may be mentioned ethylene, trimethylene and tetramethylene radicals.
  • the alkyl radicals represented by R are preferably lower alkyl radicals such as methyl, ethyl, propyl and butyl radicals.
  • the hydroxyalkyl radicals represented by R are preferably hydroxy lower alkyl radicals such as fi-hydroxyethyl and 13- or 'y-hydroxypropyl radicals.
  • alkoxyalkyl radicals represented by R are preferably lower 3,410,821 Patented Nov. 12, 1968 'ice alkoxy lower alkyl radicals such as fl-ethoxyethyl, ,8- methoxyethyl, and [ior 'y-ethoxypropyl radicals.
  • lower alkyl and lower alkoxy are used to denote alkyl and alkoxy radicals respectively containing from 1 to 4 carbon atoms.
  • radicals A and B there may be mentioned chlorine, bromine, lower alkyl in particular methyl, lower alkoxy in particular methoxy and ethoxy, nitro and cyano.
  • the process of the invention can be conveniently carried out by incorporating one or more of the said dyestuffs into the synthetic linear polyesters by any of the known techniques for mass coloration of such materials.
  • the dyestutf in finely divided form may be coated onto chips of the polyester by tumbling and the resulting coloured mixture subsequently melted and spun into filaments or shaped into solid objects.
  • tumbling may be carried out with a dispersion of the dyestuif in a volatile liquid e.g. water or alcohol, or such a liquid may be used to moisten the mixture of dyestuff and polymer during the stage of tumbling.
  • the volatile liquid is preferably removed by evaporation before melting.
  • the dyestuff may also be incorporated with monomers or prepolymers at any convenient stage in the preparation of the polyester.
  • those dyestuffs which contain a carboxylic acid group can be used in the form of salts, such :as the ammonium salts, which give rise to the free acids during the heat treatment required to melt the polyester.
  • polyesters which are obtained by the reaction of terephthalic acid with glycols of the formula wherein x is an integer of from 2 to 10, or with 1:4-di (hydroxymethyl)cyclohexane.
  • synthetic linear polyesters also includes copolyesters based on the said polyesters, such copolyesters being obtained by replacing a portion of the terephthalic acid by another dicarboxylic acid or by a hydroxycarboxylic acid, and/or replacing a portion of the glycol by a different glycol.
  • the colorations produced by the process of the invention have good fastness to washing, pressure steaming, acid cross dyeing, perspiration, rubbing after steaming, dry heat treatments such as are used in pleating operations, and to light. It is also found that the colorations can be produced in heavy depths of shade, without impairing the properties of the synthetic linear polyesters or fibres derived therefrom.
  • the dyestuffs used in the process of the invention may themselves be obtained by condensing a diamine of the formula /NH2 A NHz with an anhydride of a dicarboxylic acid of the formula ooon wherein A and B have the meanings stated, the said compounds together containing one or two -(COX--) -COOR groups.
  • diamines there may be mentioned l :2-phenylenediarnine, 4-chloro-l :Z-phenylenediamine, 4-nitro-1:Z-phenylenediamine, l:2, 2:3- or 1:8- naphthylenediamine, 3:4-diaminobenzoic acid and 4- methyl-1:Z-phenylenediamine.
  • phthalic anhydride 4-chlorophthalic anhydride, 4-bromophthalic anhydride, 4 6 7-tetrabrornophthalic anhydride, 4-nitrophthalic anhydride, trimellitic anhydride, 3-carboxyphthalic anhydride, 4-carbomethoxyphthalic anhydride, lz8-naphthalic anhydride, 1:8-naphthalic anhydride 4-carboxylic acid and 4-(o-carboxybenzoy1)-1:8-naphthalic anhydride.
  • the dyestuffs which contain the carboxylic acid group attached through an alkyl-CO- or phenyl-CO- group may be obtained by reacting the corresponding dyestulTs free from such groups with an alkylene or phenyl dicarboxylic acid in a Friedel-Crafts reaction.
  • those dyestuffs which contain a carboxylic acid ester group can be obtained by esterifying the corresponding dyestuff containing a carboxylic acid group with the appropriate alcohol.
  • Example 1 1 part of 9- and/ or -carboxyphthaloperinone in powder form is tumbled with 100 parts of polyethylene terephthalate in the form of chips. The resulting mixture is then melt spun in known manner to yield fibres of a bright orange red shade possessing excellent fastness properties.
  • the 9- and/or 10-carboxyphthaloperinone used in the above example was obtained by condensing 1 molecular proportion of 1:8-naphthylenediamine with 1 molecular proportion of trimellitic anhydride (4-carboxyphthalic anhydride).
  • Example 2 In place of the 1 part of the dyestutf used in Example 1 there is used 1 part of 8- and/or ll-carboxyphthaloperinone when yellowish-red fibres are obtained possessing excellent fastness properties.
  • the 8- and/or 1l-carboxyphthaloperinone was itself obtained by condensing 1 molecular proportion of 3-carboxyphthalic anhydride with 1 molecular proportion of 1 S-naphthylenediamine.
  • Example 3 In place of the 1 part of the dyestufl? used in Example 1 there is used 1 part of 3-(o-carboxybenzoyl)-phthaloperinone or 1 part of 3-(o-carboxybenzoyl)-8:9:10:11-
  • Example 4 parts of dimethyl terephthalate, 71 parts of ethylene glycol and 0.05 part of manganese acetate are stirred together for 4 hours at 197 C., during which time about 33 parts of methanol distil off from the mixture. To this mixture is then added 0.04 part of phosphorous acid and 005 part of antimony trioxide and 3 parts of methylphthaloperinone 9- and/or 10-carboxylate which has previously been wetted out by ball milling for 30 minutes in the presence of 12 parts of ethylene glycol. The temperature of the mixture is then increased to 277 C. and the pressure is reduced to 0.3 mm. of mercury and the heating is continued under these conditions for a further 6 hours, whilst the excess ethylene glycol distils off. The melt is then formed into filaments which are subsequently drawn out into fibres. The fibres so obtained are coloured a deep orange shade possessing excellent fastness properties.
  • Example 5 100 parts of dimethyl terephthalate, 71 parts of ethylene glycol, 0.05 part of manganese acetate and 3 parts of methyl phthaloperinone 9- and/ or IO-carboxylate are stirred for 4 hours at 197 C, during which time about 33 parts of methanol are distilled oil. 004 part of phosphorous acid and 0.05 part of antimony trioxide are added, the temperature of the mixture is then in creased to 277 C., the pressure is reduced to 0.3 mm. of mercury and heating is continued under these conditions for a further 6 hours whilst the excess ethylene glycol is distilled oil. The mixture is then formed into filaments which are subsequently drawn out into fibres. The resulting fibres are coloured a deep orange shade possessing excellent fastness properties.
  • methyl phthaloperinone 9- and/or l0-carboxylate used in the above example was obtained by heating a mixture of 7.9 parts of 1:8-naphthylenediamine and 9.7 parts of trimellitic anhydride 4-methylester (4-carbomethoxyphthalic anhydride) at 250 to 280 C. until evolution of water had ceased.
  • Example Dyestufi Shade 6 (0-carb0XybenZ0y1)829:10:11tetra.ch10rophthaloperinone R d, 7 3-(o-carboxybenzoyl)-811l-dichlorophthaloperinone Orange-red. 8 3-(ocarboxybenz0yl)-9and/or l0-carboxyphthaloperinone. Red. 9 3-(o-earboxybenzoyl)9-and/or l0-nitrophthaloperinone Red. 10 346-carboxypropionyl)phthaloperinone Brown. 11 9- and/or IO-earboxynaphthoylene henziminaz0le Yellow.
  • the 3-(o-carboxybenz0yl)phthaloperinone was itself obtained by stirring a mixture of 42 parts of phthaloperinone, 23.5 parts of phthalic anhydride, 235 parts of aluminum chloride, 23.5 parts of sodium chloride and 31 parts of potassium chloride for 1 hour at to C. The mixture was then added to 2000 parts of a 5% aqueous solution of hydrochloric acid, and the precipitated dyestuff was filtered off, washed with water and dried.
  • the 3-(0 carboxybenzoyl) 8:9:10211 tetrabromophthaloperinone was itself obtained by a similar method starting from 91 parts of 8:9:10:ll-tetrabromophthaloperinone instead of the 42 parts of phthaloperinone.
  • Example 21 In place of the 1 part of the dyestufi used in Example 1 there is used 1 part of the dyestufi of the formula:
  • the dyestufi used in this example was obtained by condensmg together equimolecular proportions of 5:6-diamlnoacenaphthene and 4-carboxyphthalic anhydride.
  • the dyestuffs used in Examples 6 to 9, which all contained a 3-(o-carboxybenzoyl) group, were obtained by condensing 8:9:10:11-tetrachlorophthaloperinone, 8:11- dichlorophthaloperinone, 9- and/ or IO-carboxyphthaloperinone or 9- and/ or lO-nitrophthaloperinone respectively wit-h phthalic anhydride at 130 C. in the presence of aluminium chloride, sodium chloride and potassium chloride.
  • the 3-(B-carboxypropionyl)phthaloperinone used in Example 10 was obtained by condensing phthaloperinone with succinic anhydride at 130 C. in the presence of aluminium chloride, sodium chloride and potassium chloride.
  • the dyestuff, or mixture of dyestuffs used in Example 11 was obtained by condensing together equimolecular proportions of 3:4-diaminobenzoic acid and 1:8-naphthalic anhydride in boiling acetic acid.
  • the dyestuifs used in Examples 12 to 14 were prepared in similar manner from equimolecular proportions of o-phenylenediamine and naphthalene 1:4:5:8-tetracarb0xylic acid, 4-methyl-ophenylenediamine and 4-carboxy-1 :S-naphthalic anhydride and 4-nitro-o-phenylenediamine and 4-carboxy-1:8- naphthalic anhydride respectively.
  • the dyestuifs used in Examples 15 and 16 were obtained by condensing naphthoylenebenziminazole with phthalic anhydride or succinic anhydride respectively at 140- C. in the presence of aluminium chloride, sodium chloride and potassium chloride.
  • the dyestuffs used in Examples 17 to 19 were obtained by reacting with ethylene chlorohydrin the sodium salt of the corresponding carboxylic acid.
  • the dyestuff used in Example 20 was obtained by treating 9- and/or 10-carboxyphthaloperinone with thionyl chloride and reacting the resulting acid chloride with B- ethoxyethanol.
  • Process for the mass coloration of synthetic linear polyesters which comprises mixing at least one dyestuif of the formula wherein one of A and B represents a 1:2 phenylene radical, and the other of A and B is selected from the class consisting of 1:2 phenylene, 1:8 naphthylene and 1:8 acenaphthylene radicals, and the said radicals contain from 1 to 2 groups of the formula wherein R is selected from the class consisting of hydrogen, lower alkyl having 1-4 carbon atoms, hydroxy lower alkyl having 1-4 carbon atoms and lower alkoxy lower alkyl wherein each of the alkoxy and alkyl moieties has 14 carbon atoms;
  • X is selected from the class consisting of lower alkylene having 1-6 carbon atoms and phenylene; n is a positive integer from 1 to 2; and any further substituents on A and B are selected from the class consisting of chlorine, bromine, nitro and lower alkyl having 1-4 carbon atoms, with the said polyester and subsequently melting the mixture and shaping it into a solid object.
  • Process for the mass coloration of synthetic linear polyesters which comprises mixing with the polyester forming ingredients at least one dyestufii of the formula 0 naphthylene radicals, and the said radicals contain from 1 to 2 groups of the formula -(COX),, COOR wherein R is selected from the class consisting of hydrogen, lower alkyl having 1-4 carbon atoms, hydroxy lower alkyl having 14 carbon atoms and lower alkoxy lower alkyl wherein each of the alkoxy and alkyl moieties has 1-4 carbon atoms;
  • X is selected from the class consisting of lower alkylene having 1-6 carbon atoms and phenylene; n is a positive integer from 1 to 2; and any further substituents on A and B are selected from the class consisting of chlorine, bromine, nitro and lower alkyl having 14 carbon atoms, and then polymerizing said mixture to produce the mass colored synthetic linear polyester.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Coloring (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US535662A 1965-03-26 1966-03-21 Mass-coloration for polyester resins Expired - Lifetime US3410821A (en)

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GB12958/65A GB1094528A (en) 1965-03-26 1965-03-26 Mass-coloration of linear polyesters

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FR (1) FR1472645A (enrdf_load_stackoverflow)
GB (1) GB1094528A (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4417014A (en) * 1979-10-25 1983-11-22 Sandoz Ltd. Phthaloperinone dyes and the use thereof for more dyeing plastics

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0104229D0 (en) * 2001-02-21 2001-04-11 Clariant Int Ltd New dye compounds

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2955902A (en) * 1955-07-20 1960-10-11 Sandoz Ag Process for the dyeing of polyester fibers
US3036077A (en) * 1958-12-22 1962-05-22 Ciba Ltd Aminobenzanthrone dyestuffs
US3103403A (en) * 1963-09-10 Dyeing of polyester fibers with com-
US3104233A (en) * 1958-06-11 1963-09-17 Ciba Ltd Process for coloring high melting organic spinning masses with colored polycyclic aromatic hydrocarbons or halogen hydrocarbons
US3228780A (en) * 1958-11-14 1966-01-11 Ciba Ltd High molecular organic products colored with a pigment dyestuff
US3242179A (en) * 1966-03-22 Perimidone-g,y-dicareoxylic imides, their production and use as pigment dyes

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3103403A (en) * 1963-09-10 Dyeing of polyester fibers with com-
US3242179A (en) * 1966-03-22 Perimidone-g,y-dicareoxylic imides, their production and use as pigment dyes
US2955902A (en) * 1955-07-20 1960-10-11 Sandoz Ag Process for the dyeing of polyester fibers
US3104233A (en) * 1958-06-11 1963-09-17 Ciba Ltd Process for coloring high melting organic spinning masses with colored polycyclic aromatic hydrocarbons or halogen hydrocarbons
US3228780A (en) * 1958-11-14 1966-01-11 Ciba Ltd High molecular organic products colored with a pigment dyestuff
US3036077A (en) * 1958-12-22 1962-05-22 Ciba Ltd Aminobenzanthrone dyestuffs

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4417014A (en) * 1979-10-25 1983-11-22 Sandoz Ltd. Phthaloperinone dyes and the use thereof for more dyeing plastics

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FR1472645A (enrdf_load_stackoverflow) 1967-05-24

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